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Volumn , Issue 2, 1998, Pages 186-194

A general synthesis of quinoline-2,5,8(1H)-triones via acylation of 2,5- dimethoxyaniline with S-tert-butyl thioacetates by application of the Knorr cyclization

Author keywords

2,5 dimethoxyanilides; Knorr cyclization; Quinoline 2,5,8(1H) triones; Regioselective alkylation; oxo thioesters

Indexed keywords

2,5 DIMETHOXYANILINE; QUINOLIN 2,5,8(1H) TRIONE; QUINOLINE DERIVATIVE; S TERT BUTYL ACETOTHIOACETATE; THYMIDYLATE SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0031889616     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2014     Document Type: Article
Times cited : (20)

References (42)
  • 23
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    • (1983) Tetrahedron Lett. , vol.24 , pp. 5143
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  • 26
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    • Aryllead triacetates give 2,2-disubstituted derivatives by treatment with the anions derived from several types of β- dicarbonyl compounds. See, for example: Rowe, B. A.; Pinhey, J. T. Aust. J. Chem. 1979, 32, 1561.
    • (1979) Aust. J. Chem. , vol.32 , pp. 1561
    • Rowe, B.A.1    Pinhey, J.T.2
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    • Dialkylation through this mechanism is a common problem in the reaction of enolate anions and alkyl halides. See: Jackman, L. M. Tetrahedron 1977, 33, 2737.
    • (1977) Tetrahedron , vol.33 , pp. 2737
    • Jackman, L.M.1
  • 29
    • 0002782655 scopus 로고
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    • Caine, D. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford 1991; Vol. 3, p 1.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 1
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  • 34
    • 34548004250 scopus 로고    scopus 로고
    • note
    • Compound 18 had been previously prepared from 2,5-dimethoxyaniline and 2,2,6-trimethyl-1,3-dioxin-4-one. See ref 4a.
  • 36
    • 0000271393 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford
    • Similar oxygen additions to other enols and enolates are described: Jones, A. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford 1991; Vol. 7, p 151.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 151
    • Jones, A.B.1
  • 37
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    • We have observed a similar oxidative degradation in the absence of metals for 3-aryl-β- oxo anilides, which exist predominantly as enol tautomers. López-Alvarado, P.; Avendaño, C.; Menéndez, J. C. J. Org. Chem. 1996, 61, 5865.
    • (1996) J. Org. Chem. , vol.61 , pp. 5865
    • López-Alvarado, P.1    Avendaño, C.2    Menéndez, J.C.3
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    • note
    • 4).
  • 40
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    • note
    • 2].
  • 42
    • 34548003394 scopus 로고    scopus 로고
    • note
    • The reaction was complete after 1.5 h in most cases. However, if the mixture is quenched in this moment, the yield obtained is lower because silver species in solution interfere during the purification process.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.